Popular smoking articles, such as cigarettes, have a substantially cylindrical rod shaped structure and include a charge, roll or column of smokable material such as shredded tobacco (e.g., in cut filler form) surrounded by a paper wrapper thereby forming a so-called “tobacco rod.” Normally, a cigarette has a cylindrical filter element aligned in an end-to-end relationship with the tobacco rod. Typically, a filter element comprises plasticized cellulose acetate tow circumscribed by a paper material known as “plug wrap.” Certain cigarettes incorporate a filter element having multiple segments, and one of those segments can comprise activated charcoal particles. Typically, the filter element is attached to one end of the tobacco rod using a circumscribing wrapping material known as “tipping paper.” It also has become desirable to perforate the tipping material and plug wrap, in order to provide dilution of drawn mainstream smoke with ambient air. A cigarette is employed by a smoker by lighting one end thereof and burning the tobacco rod. The smoker then receives mainstream smoke into his/her mouth by drawing on the opposite end (e.g., the filter end) of the cigarette.
The tobacco used for cigarette manufacture is typically used in blended form. For example, certain popular tobacco blends, commonly referred to as “American blends,” comprise mixtures of flue-cured tobacco, burley tobacco, and Oriental tobacco, and in many cases, certain processed tobaccos, such as reconstituted tobacco and processed tobacco stems. The precise amount of each type of tobacco within a tobacco blend used for the manufacture of a particular cigarette brand varies from brand to brand. However, for many tobacco blends, flue-cured tobacco makes up a relatively large proportion of the blend, while Oriental tobacco makes up a relatively small proportion of the blend. See, for example, Tobacco Encyclopedia, Voges (Ed.) p. 44-45 (1984), Browne, The Design of Cigarettes, 3rd Ed., p. 43 (1990) and Tobacco Production, Chemistry and Technology, Davis et al. (Eds.) p. 346 (1999).
Through the years, various treatment methods and additives have been proposed for altering the overall character or nature of tobacco materials utilized in tobacco products. For example, additives or treatment processes have been utilized in order to alter the chemistry or sensory properties of the tobacco material, or in the case of smokable tobacco materials, to alter the chemistry or sensory properties of mainstream smoke generated by smoking articles including the tobacco material. The sensory attributes of cigarette smoke can be enhanced by incorporating flavoring materials into various components of a cigarette. Exemplary flavoring additives include menthol and products of Maillard reactions, such as pyrazines, aminosugars, and Amadori compounds. See also, Leffingwell et al., Tobacco Flavoring for Smoking Products, R.J. Reynolds Tobacco Company (1972), which is incorporated herein by reference. In some cases, treatment processes involving the use of heat can impart to the processed tobacco a desired color or visual character, desired sensory properties, or a desired physical nature or texture. Various processes for preparing flavorful and aromatic compositions for use in tobacco compositions are set forth in U.S. Pat. No. 3,424,171 to Rooker; U.S. Pat. No. 3,476,118 to Luttich; U.S. Pat. No. 4,150,677 to Osborne, Jr. et al.; U.S. Pat. No. 4,986,286 to Roberts et al.; U.S. Pat. No. 5,074,319 to White et al.; U.S. Pat. No. 5,099,862 to White et al.; U.S. Pat. No. 5,235,992 to Sensabaugh, Jr.; U.S. Pat. No. 5,301,694 to Raymond et al.; U.S. Pat. No. 6,298,858 to Coleman, III et al.; U.S. Pat. No. 6,325,860 to Coleman, III et al.; U.S. Pat. No. 6,428,624 to Coleman, III et al.; U.S. Pat. No. 6,440,223 to Dube et al.; U.S. Pat. No. 6,499,489 to Coleman, III; U.S. Pat. No. 6,591,841 to White et al.; and U.S. Pat. No. 6,695,924 to Dube et al.; and US Pat. Appl. Publication Nos. 2004/0173228 to Coleman, III and 2010/0037903 to Coleman, III et al., each of which is incorporated herein by reference. Additionally, examples of representative components that can be employed as so-called natural tar diluents in tobacco products are set in PCT WO 07/012,980 to Lipowicz, which is incorporated herein by reference.
Tobacco also may be enjoyed in a so-called “smokeless” form. Particularly popular smokeless tobacco products are employed by inserting some form of processed tobacco or tobacco-containing formulation into the mouth of the user. Various types of smokeless tobacco products are set forth in U.S. Pat. No. 1,376,586 to Schwartz; U.S. Pat. No. 3,696,917 to Levi; U.S. Pat. No. 4,513,756 to Pittman et al.; U.S. Pat. No. 4,528,993 to Sensabaugh, Jr. et al.; U.S. Pat. No. 4,624,269 to Story et al.; U.S. Pat. No. 4,987,907 to Townsend; U.S. Pat. No. 5,092,352 to Sprinkle, III et al.; U.S. Pat. No. 5,387,416 to White et al.; and U.S. Pat. No. 8,336,557 to Kumar et al.; US Pat. Appl. Pub. Nos. 2005/0244521 to Strickland et al. and 2008/0196730 to Engstrom et al.; PCT WO 04/095959 to Arnarp et al.; PCT WO 05/063060 to Atchley et al.; PCT WO 05/016036 to Bjorkholm; and PCT WO 05/041699 to Quinter et al., each of which is incorporated herein by reference. See, for example, the types of smokeless tobacco formulations, ingredients, and processing methodologies set forth in U.S. Pat. No. 6,953,040 to Atchley et al. and U.S. Pat. No. 7,032,601 to Atchley et al., each of which is incorporated herein by reference.
One type of smokeless tobacco product is referred to as “snuff.” Representative types of moist snuff products, commonly referred to as “snus,” have been manufactured in Europe, particularly in Sweden, by or through companies such as Swedish Match AB, Fiedler & Lundgren AB, Gustavus AB, Skandinavisk Tobakskompagni A/S, and Rocker Production AB. Snus products available in the U.S.A. have been marketed under the tradenames Camel Snus Frost, Camel Snus Original and Camel Snus Spice by R. J. Reynolds Tobacco Company. See also, for example, Bryzgalov et al., 1N1800 Life Cycle Assessment, Comparative Life Cycle Assessment of General Loose and Portion Snus (2005). In addition, certain quality standards associated with snus manufacture have been assembled as a so-called GothiaTek standard. Representative smokeless tobacco products also have been marketed under the tradenames Oliver Twist by House of Oliver Twist A/S; Copenhagen, Skoal, SkoalDry, Rooster, Red Seal, Husky, and Revel by U.S. Smokeless Tobacco Co.; “taboka” by Philip Morris USA; Levi Garrett, Peachy, Taylor's Pride, Kodiak, Hawken Wintergreen, Grizzly, Dental, Kentucky King, and Mammoth Cave by Conwood Company, LLC; and Camel Orbs, Camel Sticks, and Camel Strips by R. J. Reynolds Tobacco Company.
The sensory attributes of smokeless tobacco can also be enhanced by incorporation of certain flavoring materials. See, for example, U.S. Pat. No. 6,668,839 to Williams; U.S. Pat. No. 6,834,654 to Williams; U.S. Pat. No. 7,032,601 to Atchley et al.; U.S. Pat. No. 7,694,686 to Atchley et al.; U.S. Pat. No. 7,861,728 to Holton, Jr. et al.; U.S. Pat. No. 7,819,124 to Strickland et al.; U.S. Pat. No. 7,810,507 to Dube et al.; and U.S. Pat. No. 8,168,855 to Nielsen et al; US Pat. Appl. Pub. Nos. 2004/0020503 to Williams, 2006/0191548 to Strickland et al.; 2007/0062549 to Holton, Jr. et al.; 2008/0029116 to Robinson et al.; 2008/0029117 to Mua et al.; and 2008/0173317 to Robinson et al., each of which is incorporated herein by reference.
Among the many constituents of tobacco is lutein (CAS 127-40-2). See, for example, Tso, Physiology and Biochemistry of Tobacco Plants, pp. 209, 212 (1972). Lutein has a molecular weight of about 568.87 and is also known, for example, as xanthophyll; or (3R,3′R,6R)-4,5-didehydro-5,6-dihydro-β,β-carotene-3,3′-diol. While it may serve any of a number of functions in tobacco product formulations, lutein is known in the art to serve as an antioxidant, an anti-inflammatory agent, an agent to prevent and/or ameliorate age-related macular degeneration, and an agent counteracting the deleterious effects of certain polycyclic aromatic hydrocarbons subject to activation by one or more cytochrome P450 monooxygenases. At typical room temperature, lutein is yellowish in color and may have the microscopic appearance of prisms. Lutein is essentially insoluble in water and has a melting point of less than 200° C.
Methods for producing lutein are known in the art. U.S. Pat. No. 6,262,284 to Khachik teaches a method for the extraction and saponification of lutein esters from a plant source comprising extraction with a solution containing tetrahydrofuran and an alcohol with the addition of potassium or sodium hydroxide to maintain the pH at 12. U.S. Pat. No. 7,253,294 to Hoffman et al. teaches isolating lutein by inter alia heating a syrup derived from macerated alfalfa green plants, separating a solid fraction from the syrup, then extracting, saponifying and further extracting the solid fraction. U.S. Pat. No. 7,271,298 to Xu et al. teaches a process for preparing xanthophylls such as lutein comprising saponifying a plant oleoresin with an alcohol at 40-85° C. and adjusting the pH of the resultant mixture to pH 1-7. U.S. Pat. No. 7,351,424 to Ornelas-Cravioto et al. teaches inter alia a composition comprising at least 85% by weight of xanthophyll esters, wherein the xanthophyll esters are comprised of at least 94% of trans-lutein esters. U.S. Pat. No. 7,622,599 to Swaminathan et al. teaches producing lutein-enriched carteonoids by inter alia anaerobically ensilaging Marigold flower petals, hexane extraction of meal derived therefrom, and hot water washing of the extract. U.S. Pat. No. 7,629,007 to Pena teaches isolating a xanthophyll such as lutein by inter alia preparing and saponifying a plant-derived oleoresin, washing the saponified oleoresin with a salt solution until the pH of the resin is about 6.5 to 9, and washing the resin with a non-polar solvent and with an increased polarity solvent. U.S. Pat. No. 8,236,929 to Cheryan et al. teaches obtaining xanthophylls such as lutein by extracting corn with warm ethanol. U.S. Pat. No. 7,671,242 to Losso et al. teaches isolating aflatoxin-free lutein by inter alia treating a ground plant source with acetone. US Pat. Appl. Pub. No. 2012/0141648 to Morton et al. teaches homogenizing plant material in the presence of an extraction solvent to form a combination of a plant liquid component and a plant pulp component such that the plant liquid component is provided with a pH in a defined range; withdrawing the plant liquid component from the plant pulp component; and separating the liquid plant component into a solids fraction and a soluble fraction. US Pat. Appl. Pub. No. 2012/0272976 to Byrd et al. teaches a method of extracting and isolating lutein from tobacco material comprising contacting the tobacco material with a solvent for a time and under conditions sufficient to extract lutein from the plant material into the solvent; separating the solvent containing lutein from the extracted tobacco material; and purifying the solvent containing lutein to provide an isolate comprising at least about 75 percent by weight lutein. Each of the foregoing is incorporated herein by reference.
While methods for producing lutein are known in the art, facile methods for producing lutein from tobacco that do not employ extremes of temperature or pH are not. There is a long-felt need for a method for producing lutein from a plant source whose agronomic properties are well-characterized and favorable, such as tobacco, from which considerable per-plant biomass is produced during a single growing season. More generally, there is a long-felt need for an environmentally favorable process for the preparation of such a valuable constituent as lutein.
As it should be clear from the foregoing that lutein is useful not only as a constituent of various tobacco products but also an antioxidant, an anti-inflammatory agent, an agent to prevent and/or ameliorate age-related macular degeneration, and an agent counteracting the deleterious effects of certain polycyclic aromatic hydrocarbons subject to activation by one or more cytochrome P450 monooxygenases, it can also be seen that it would accordingly be desirable to provide a method for producing lutein from tobacco, that is, in particular, from Nicotiana species, for use, inter alia, in tobacco compositions utilized in a variety of tobacco products or in the processing of tobacco, or more generally in compositions that may comprise an antioxidant, an anti-inflammatory agent, an agent to prevent and/or ameliorate age-related macular degeneration, and/or an agent counteracting the deleterious effects of certain polycyclic aromatic hydrocarbons subject to activation by one or more cytochrome P450 monooxygenases.